The Last 100 Days: From Old Wounds to New Ties Edition

Ever since the administration of Franklin Delano Roosevelt, presidents have been judged on the successes they notch during their first 100 days. Now, as Barack Obama prepares to end his historic turn on the political stage, Yahoo News is running The Last 100 Days, a look at what Obama achieved during his consequential presidency, how he navigates the struggles of his last months in office and what lies ahead for him after eight years filled with firsts. We will also look at how the country bids farewell to its first African-American president.

It’s not a literal 100 days — Obama leaves office in late January 2017.

And it won’t all be about policy. As Obama himself is fond of noting, he also spent his two terms as father to daughters Malia and Sasha and husband to first lady Michelle Obama. And even without much input from the White House, the cultural landscape shifted dramatically over his two terms on issues such as gay rights.

And then there’s the way the president sees the presidency — not just his tumultuous years at 1600 Pennsylvania Ave., but also the institution and its relationships (for better or worse) with other branches of government and with the news media.

In this 14th installment, we look at Obama’s personal efforts to end, or at least diminish, some old diplomatic disputes.

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In late December, Barack Obama will do something no other sitting U.S. president has done: tour the Pearl Harbor memorial with a sitting Japanese prime minister, Shinzo Abe. The visit comes seven months after Abe played host as Obama became the first sitting U.S. president to visit the Hiroshima Peace Memorial.

Obama said he had come to that city, where the United States dropped the first of two atomic bombs, to “mourn the dead” from seven decades earlier. He offered no apology. And Abe will most likely follow that lead — mourn Americans killed in the 1941 surprise attack, but not say “sorry” — when he comes to Hawaii Dec. 26-27.

Japan and the United States have long been allies, but World War II resentments linger. The mutually reinforcing visits offer a glimpse into a feature of Obama’s diplomatic legacy: a concerted effort to pull America beyond historic feuds, reframe relationships with countries like Cuba and Burma, build on his predecessors’ outreach to countries like Vietnam and attempt a “reset” in relations with Russia.

As the curtain comes down on Obama’s consequential presidency, it’s worth looking at the ways he has both struggled and succeeded to keep a promise he made even before taking office: to turn old foes into new friends, or something close to it.

“The president is willing to engage countries that have been adversaries, break taboos in our foreign policy. [He] does not think we should be constrained — that we should do a thing because we’ve always done it this way,” Deputy National Security Adviser Ben Rhodes told Yahoo News. “Both substantively and symbolically, healing old wounds and trying to move past difficult history has been essential, especially in the second term.”

During his 2008 campaign, Obama faced criticism for two very different promises. First, he swore he’d unleash American military might to take out Osama bin Laden if the al-Qaida leader were found to be hiding in Pakistan, whether or not that ally approved. Second, he pledged his willingness to sit down for talks with leaders of Iran, Syria, Venezuela, Cuba and North Korea, without preconditions. For the first, Obama’s critics called him reckless; for the second, naive.

But he stuck to both themes. His 2009 Nobel Peace Prize acceptance speech included an unapologetic vow to use force unilaterally if necessary. And his 2009 inaugural address included an olive branch to nations at odds with America. “To those who cling to power through corruption and deceit and the silencing of dissent, know that you are on the wrong side of history, but that we will extend a hand if you are willing to unclench your fist,” he said.

Later in the year, Obama delivered a speech in Cairo to offer the Muslim world “a new beginning” in ties with Washington, a fresh relationship “based on mutual interest and mutual respect.” The subtext of the speech was that Obama was not George W. Bush, who had seen U.S. relations with the region largely through the prism of the global war on terrorism he declared after 9/11 — including the 2003 invasion of Iraq.

Now, seven years later, relations with the region are transformed, but not because of Obama’s outreach. The tumultuous “Arab Spring” of 2011 toppled some of the region’s strongmen. Libya’s Moammar Gadhafi is gone, pushed out by rebels aided by the United States and its NATO partners. Protesters ousted Egypt’s Hosni Mubarak, a crucial U.S. ally for decades, and the latest Egyptian president, Abdel Fattah el-Sisi, has cracked down on dissent and nongovernmental organizations. Obama takes frequent criticism for not doing more to stop Syria’s bloody civil war, with a death toll of as many as 400,000. After withdrawing U.S. troops from Iraq in 2011 — a step he still regards as a legacy-defining achievement — Obama hurried thousands back to counter the rise of the so-called Islamic State. And Middle East peace seems as far away as ever.

“We’d hoped to get further toward overcoming the history of the Israel-Palestinian conflict,” Rhodes told Yahoo News.

But Obama seems to have pushed past history in the U.S. relationship with Cuba. The president and his Cuban counterpart, Raúl Castro, stunned the world in December 2014 by announcing that they had agreed after months of secret talks to work toward closer relations. But Obama had worked for years to ease U.S. pressure off Havana, making it easier for Cuban-Americans to send money to relatives on the island and visit them, for example.

Rhodes, one of the key U.S. negotiators with Havana, said “part of what the president instructed me to say was, ‘We’re not going to be bound by this past Cold War standoff, or grudge, where our relationship is just a recitation of a series of grievances in each direction.’”

It’s not clear whether President-elect Donald Trump will roll back Obama’s outreach — reversing executive actions that made it easier for Americans to travel to Cuba, spend money there, and return with cigars and rum. The entrepreneur recently said he would “terminate” the deal unless the government in Havana undertakes unspecified steps to benefit its people and those in the U.S. Obama aides say they think they have created enough opportunities for U.S. businesses and American visitors in Cuba that the deal may be “irreversible.”

Republicans have portrayed the arrangement as Obama making concessions — giving the Castro regime access to foreign currency it needs to buy imports — without getting anything by way of democratic reforms in return. They note that most tourism earnings land in the military’s pockets.

Obama aides argue that Cuban entrepreneurs are benefiting from the arrangement, which boosts the island’s new restaurateurs, cabdrivers and those who make their homes available to visitors on Airbnb. And Obama’s team says the six-decade U.S. embargo, which Obama cannot lift without congressional action, only served to give the Castro regime a scapegoat for economic hardships.

The recent death of Fidel Castro has highlighted another aspect of Obama’s softer approach with Havana. Some U.S. officials say privately that a big part of the strategy has to do with reassuring Cubans that the island has a post-Castro economic future. Cubans without any prospects might decide to chance coming to the United States, where the Florida coast is just 90 miles away, rather than face a potentially chaotic succession.

At the same time, the White House has admitted that Cuba may follow the Vietnam model: embracing the economic and strategic benefits of closer ties with the United States without enacting significant democratic reforms.

When it comes to the relationship between Washington and Hanoi, Obama built on two decades of presidential diplomacy that enjoys bipartisan support in Congress. It was Bill Clinton who ended the U.S. trade embargo in 1994 and restored diplomatic relations in 1995. George W. Bush visited the country in 2006 and promised deeper ties while pushing greater religious freedom.

Obama visited Vietnam in May, when he lifted an embargo on arms sales that dated back to the aftermath of the war and visited the home of the country’s revolutionary leader, Ho Chi Minh.

“I come here mindful of the past, mindful of our difficult history, but focused on the future — the prosperity, security and human dignity that we can advance together,” he said.

Obama’s acknowledgments of the scars of the conflict “had a cleansing effect,” Rhodes said. They helped to enable Vietnam “to say, ‘Well, maybe now we can pursue greater military cooperation with the United States.’”

Vietnam wasn’t the only Southeast Asian country Obama courted during his eight years in office. Starting in late 2011, his administration worked to improve relations with Burma (also known as Myanmar). In November 2012, he became the first sitting U.S. president to visit that country.

“It was risky,” Rhodes said.

And political and economic reforms have been uneven, even though the country earlier this year replaced military leaders with its first civilian president in five decades. Burma’s iconic democracy champion Aung San Suu Kyi is no longer under house arrest but cannot serve in the top executive branch spot due to the military-drafted constitution.

Still, Obama’s outreach gets praise from Republicans in Congress, including the top expert on U.S.-Burma relations, Senate Majority Leader Mitch McConnell.

“Burma’s transition to a democratically elected government is an important mark of reform in a country with a long and very troubled history,” McConnell said earlier this year. “We know there’s more to be done, but the administration can take credit for its efforts and so can members of Congress in both parties. Hopefully we can build on that momentum by working together.”

That kind of bipartisanship goes missing when it comes to Obama’s “reset” of relations with Russia. That 2009 reboot of the way Washington and Moscow interact paid some early dividends, notably Russian acceptance of a new START treaty to reduce nuclear arsenals, greater cooperation on sanctions against Iran and the reopening of air routes to resupply American forces in Afghanistan.

But the policy was in tatters even before the recent bombshell Washington Post report that Russia actively worked to get Trump elected. President Vladimir Putin openly fueled anti-American sentiment at home and pursued confrontational policies abroad, such as the invasion of Ukraine and the annexation of its Crimea region. One of the key architects of the U.S. policy, former ambassador to Russia Michael McFaul, said in May 2015 that the next president should not try to duplicate it.

“With Russia, we got a long way with [former Russian President Dmitry] Medvedev, and then engagement hit a brick wall when we went from Medvedev to Putin,” Rhodes said.

It might be tempting to look at the Iran nuclear deal in the broader context of Obama’s foreign engagement. But Rhodes said the agreement wasn’t designed to transform relations.

“The Burmese decided to change their political system. The Cubans decided to engage and make some changes to their economic system. Iran did not make a similar decision,” he said. “Iran made a decision to make a deal on the nuclear issue, but we don’t expect them to fundamentally alter their system or their behavior.”

Likewise, the symbolic setting aside of World War II grievances with Japan isn’t expected to fundamentally alter relations between the two allies.

“The president is of the view that — as he has done with American history — the candid accounting of history is a necessary first step,” Rhodes said. “It’s just one of the pieces of unfinished business.”